


Fun with Fantasies

by Mayghan1



Series: Fun [2]
Category: Critical Role (Web Series)
Genre: Alternate Universe - Modern with Magic, Campaign 1 (Critical Role), F/M, M/M, Multi, Not Beta Read, Polyamory
Language: English
Status: In-Progress
Published: 2020-12-30
Updated: 2020-12-30
Packaged: 2021-03-11 01:53:27
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,469
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28437174
Author URL: https://archiveofourown.org/users/Mayghan1/pseuds/Mayghan1
Summary: Jester knows her fiancé has a fantasy.  Is it possible to make this work for everyone
Relationships: Beauregard Lionett/Yasha, Fjord & Mollymauk Tealeaf, Jester Lavorre/Caleb Widogast
Series: Fun [2]
Series URL: https://archiveofourown.org/series/2082963
Comments: 2
Kudos: 12





	Fun with Fantasies

**Author's Note:**

> Sequel to Fun with Gold Dust, but not necessary to read  
> This will become adult rated later.

On the drive home from Traveler Con that weekend Jester looked at Caleb. "Who is your fantasy lover?"

' _Schatz_ , I love you but if I tell you, you will pull do anything to make it happen."

"To make you happy, of course. What's wrong with that?" She asked.

"Nothing, if he were interested, and I don't know that he is. And even he is interested in me, that doesn't mean he would be interested in a threesome." Caleb explained gently.

Jester nodded. "Okay I understand that, but what if he is interested? Even without me? Would you want that?"

Caleb had a little shiver at the thought. "Jester, I won't lie to you. Yes, I would like that, and I would prefer it to be you both sharing me, but I can't say I would say no to private time with him, as long as I could be guaranteed it wouldn't hurt you."

"As long as I know who it is, and you told me it was happening, I am positive it wouldn't bother n me as wel at all."

"Jester, I don't see it happening. I don't believe he is interested, and it's not worth it."

The woman let out a frustrated sigh, she knew her fiancé was stubborn. If he didn't want to tell her, he wasn't going to. "Fine, I will drop it, but make me a deal."

"I will try." Caleb allowed, knowing better than agreeing without all the information.

"If I guess it who he is, you will tell me if I am right."

Caleb smiled, this was a fair deal. While Jester knew the man in question, he would not easily come to mind in this conversation. "Yes, I think that is acceptable."

Jester smiled victoriously. "Yay! Are there any other ground rules for my guesses?"

"He's not married, and you know this man. That is as much as I am willing to narrow it down for you."

Jester nodded. "And I will add this rule as well, if I don't have it figured out by the time we go to be bed tonight, then I get one guess a day only."

Caleb chuckled, "Deal."

Jester squealed excitedly. "Okay unmarried. So Yeza, Percy and Vax are out. Caduceus is obviously out."

Caleb nodded, as she excluded friends and acquaintances. Frankly her exclusions had her closer than Caleb expected on day one, but he wasn't going to admit that.

"Fjord?" Was her first guess.

"If I agreed to this game, why would I make it so easy by it being my ex-roommate, and one of my closest friends,"

Jester shrugged. "Hiding in plain sight?" She guessed.

"Not in this case." Caleb told her.

"Am I getting warm?"

"That wasn't part of my our ground rules." Caleb pointed out, even though the answer was a hard no.

"Mollymauk?" Jester guessed.

Caleb let out a bark of laughter. "What kind of man do you think I am if I coveted my close friend's lover?"

"A human?" Jester suggested. "Molly and Fjord are good together, but not married. So he falls under the rules." She pointed out, then paused. "However you did say you are unsure if this person was a interested in you. You'd have to be blind not to see the interest in Molly's eyes."

"Or our favorite peacock is just plain a flirt? However even if he is attractive, and lovely. It is not Mr. Tealeaf."

It had been a month since that conversation, and Jester was still narrowing down her guesses. She didn't guess everyday, and she always made sure the guesses she did make was later in the day. This evening, Jester and Caleb were getting ready for a fund raiser at the Cobalt Soul Library. While both of them were big believers in the library and donated both money and time as often as they possibly could, tonight was a little different.

Tonight's party was the first event ran solely by Beauregard Lionett, Jester's best friend. Beau was the newest expositor librarian at the Cobalt Soul. Part of her duties was to organize donations and volunteers. This party, however was to honor one of the biggest benefactors of the year. Jester had volunteered her time to decorate the hall, Caduceus had been hired to cater the dinner, as well as tea service.

Caleb was looking a little nervous when they got out of his car to walk across the street to the library,

"Is something. wrong?" Jester asked, lacing her fingers with his.

"No, just a long day at work today. I don't see tomorrow being any better. Especially if Ikithon hears, I had fun anytime in my life." Caleb quipped, speaking of his boss. The man was really critical of most of his employees, but Trent Ikithon was more so to Caleb mainly because he had rebuffed his boss' offer to groom him as his successor. And to add insult to injury, Caleb was friends with other magic users, who had offered him jobs before, and Caleb was getting closer and closer to agreeing to the offer.

Jester laughed at the sarcastic remark. "Will he be here?" She asked of Caleb's boss. He was influential yes, but friendly was not an adjective that should be used. Also the honoree of the evening was hated almost as much as Caleb.

Caleb smirked. "I heard him today, very angry with Astrid, that she didn't secure him an invite. So Astrid had to call the Library today and apparently got ahold of Beau. And Beau told Astrid in no uncertain turns, it was not an oversight, and besides it was past the RSVP deadline, so there was no room."

Jester laughed at her best friend's bluntness. "I am sure Beau enjoyed every minute of it."

" _Ja_ , I am sure as well. But that just means he is going to be so much worse tomorrow."

Jester patted his hand, sympathetically. "But he does know who this is honoring, right?"

" Yes, I think that was part of the reason he wanted to be here, just to wreak havoc."

"But I am guessing it wasn't Beau who actually blackballed Trent tonight."

"I agree, but Beau loved being to the one to say 'sorry ,not sorry.'" Caleb pointed out, then looked up as a tall woman all but ran up on them.

"Oh, thank the gods, you're here." She said, turning to walk with them.

"Hi Yasha." Jester greeted, "Is there a problem?" She asked, although the question sounded bizarre. Yasha was a trained bodyguard and could handle herself. However, she was an introvert, so the problem could very well be being by herself in a large group of strangers, or near strangers.. Truthfully the only reason she was probably here, instead of working on a photo album at home, was it was a big night for Beau. Yasha would sacrifice herself to support her girlfriend.

"Not technically." Yasha sighed. "But Beau is going to be busy all night, and I don't like mingling alone. Can I hang out with you guys for awhile. Molly and Fjord aren't here, yet. Caduceus is just as busy as Beau, and Veth..." She trailed off, realizing Caleb would know more about Veth and she suddenly felt self-conscious talking about Caleb's best friend.

"Veth and Yeza are not going to be here tonight. They decided to stay home with Luc." Caleb supplied, "But of course, you are welcome to spend time with us. " He told their friend.

Yasha sighed, in relief. "Thanks. By the way, we are all sitting at the main table."

'Jester looked at her friend. "But why? None of us are the MC or Honorees." Her voice was a couple octaves higher than usual.

Yasha smiled. "Caleb and I are sitting at the table as plus ones.; Beau is the MC so obviously she is there. And Jester, you decorated this place so it's a reward to you. And you did a beautiful job by the way" She explained, and walked them to their seats.

"Yes, it looks beautiful in here" Caleb questioned, agreed, then whispered in her ear, "How many dicks are hidden in the room?"

Jester giggles giggled and shrugged. "You'll have to look and see for yourself." She replied.

"Caleb! Jester! It's lovely to see you!" A voice said, spinning Caleb into a hug and kissed both of his cheeks. He moved to Jester next and spun her into a hug. After a quick greeting, he then buzzed over to talk to other people who entered the hall.

Jester's eyes grew larger, and she cuddled close to her fiancé, and whispered in his ear. "It's Shaun Gilmore."

Caleb smiled indulgently. " _Ja, Schatz,_ I thought you knew he was the benefactor and guest of honor this evening." He said confused.

"No, Cayleb. You want Shaun Gilmore."

**Author's Note:**

> I should apologize for a cliffhanger I know, but not that sorry.  
> Bonus about modern AU is I can play with a rare pair that probably would not be logical canonically.
> 
> As always, love and comments gets things coming out faster.


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